Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 67250154 | HCID 67250154 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 57949706 | HCID 57949706 | 19% |
Reaction Steps
A mixture of 6-fluoro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-one (0.100 g, 0.22 mmol), PdCl2(dppf)2 (0.008 g, 0.011 mmol), zinc cyanide (0.051 g, 0.44 mmol), and zinc (0.007 g, 0.011 mmol) in DMF (5 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate afforded 5-fluoro-3-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile (0.015 g, 19%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.31 (s, 2H), 4.81 (s, 2H), 7.19 (d, 2H), 7.37 (m, 3H), 7.64 (m, 1H). GC-MS: m/z 350 (M)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968570B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-980c205505094568a1effeb4b8a530b1 |
|---|
| Source note | uspto-grants-2011_06 |
|---|
